JPH026436A - 適宜なハロゲノビニル誘導体から出発するトリフルオルメチルビニル誘導体の新規の製造方法 - Google Patents
適宜なハロゲノビニル誘導体から出発するトリフルオルメチルビニル誘導体の新規の製造方法Info
- Publication number
- JPH026436A JPH026436A JP1078715A JP7871589A JPH026436A JP H026436 A JPH026436 A JP H026436A JP 1078715 A JP1078715 A JP 1078715A JP 7871589 A JP7871589 A JP 7871589A JP H026436 A JPH026436 A JP H026436A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- carbon atoms
- tables
- formulas
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 238000000034 method Methods 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 25
- 125000005843 halogen group Chemical group 0.000 claims abstract description 16
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 71
- 239000000203 mixture Substances 0.000 claims description 63
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- 239000000126 substance Substances 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 21
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- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
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- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
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- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 claims description 4
- AFEOKIGLYCQHAZ-UHFFFAOYSA-N (5-benzylfuran-3-yl)methanol Chemical compound OCC1=COC(CC=2C=CC=CC=2)=C1 AFEOKIGLYCQHAZ-UHFFFAOYSA-N 0.000 claims description 4
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 4
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- 150000003839 salts Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
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- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 244000000054 animal parasite Species 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 208000005687 scabies Diseases 0.000 claims description 2
- 125000001174 sulfone group Chemical group 0.000 claims description 2
- 125000003375 sulfoxide group Chemical group 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 150000001879 copper Chemical class 0.000 claims 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 claims 1
- QQHOVRKETYPQHY-UHFFFAOYSA-N 2-(hydroxymethyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound O=C1N(CO)C(=O)C2=C1CCCC2 QQHOVRKETYPQHY-UHFFFAOYSA-N 0.000 claims 1
- AFJWMGOTLUUGHF-UHFFFAOYSA-N 4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1CCCC2=C1C(=O)NC2=O AFJWMGOTLUUGHF-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract description 6
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- 239000003480 eluent Substances 0.000 description 8
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- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- 239000000377 silicon dioxide Substances 0.000 description 6
- 239000013543 active substance Substances 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
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- 241001481703 Rhipicephalus <genus> Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/647—One oxygen atom attached in position 2 or 6 and having in the molecule an acyl radical containing a saturated three-membered ring, e.g. chrysanthemumic acid esters
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Animal Husbandry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Food Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR88-04260 | 1988-03-31 | ||
| FR8804260A FR2629452B1 (fr) | 1988-03-31 | 1988-03-31 | Nouveau procede de preparation de derives trifluoromethylvinyliques a partir de derives halogenovinyliques correspondants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH026436A true JPH026436A (ja) | 1990-01-10 |
Family
ID=9364830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1078715A Pending JPH026436A (ja) | 1988-03-31 | 1989-03-31 | 適宜なハロゲノビニル誘導体から出発するトリフルオルメチルビニル誘導体の新規の製造方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US4920231A (de) |
| EP (2) | EP0476708B1 (de) |
| JP (1) | JPH026436A (de) |
| CN (1) | CN1023476C (de) |
| AT (1) | ATE129999T1 (de) |
| AU (1) | AU622160B2 (de) |
| BR (1) | BR8901489A (de) |
| DE (2) | DE68906703T2 (de) |
| ES (2) | ES2042021T3 (de) |
| FR (1) | FR2629452B1 (de) |
| GR (1) | GR3008401T3 (de) |
| IE (1) | IE63711B1 (de) |
| MX (1) | MX173047B (de) |
| NZ (1) | NZ228536A (de) |
| ZA (1) | ZA892010B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3820895A1 (de) * | 1988-06-21 | 1989-12-28 | Basf Ag | Pyrethroide, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
| FR2658820B1 (fr) * | 1990-02-27 | 1994-06-03 | Roussel Uclaf | Nouveaux derives du pyrrole, leur procede de preparation et leur application comme pesticides. |
| FR2658819B1 (fr) * | 1990-02-27 | 1993-03-12 | Roussel Uclaf | Nouveaux esters derives d'acide 3-(2-cyano 2-halogeno ethenyl) 2,2-dimethyl cyclopropanecarboxylique, leur procede de preparation et leur application comme pesticides. |
| JPH06239712A (ja) * | 1993-02-19 | 1994-08-30 | Sumitomo Chem Co Ltd | 土壌害虫防除剤 |
| KR100787808B1 (ko) | 2006-12-22 | 2007-12-21 | (주)제이브이엠 | 도어락킹부를 갖는 약제 자동 포장기 |
| GB2607741B (en) | 2017-11-30 | 2023-03-29 | Axalta Coating Systems Gmbh | Coating compositions for application utilizing a high transfer efficiency applicator and methods and systems thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55154943A (en) * | 1979-05-23 | 1980-12-02 | Bayer Ag | 22phenyllalkk11enyllcyclopropaneecarboxylic acid ester* its manufacture* use as insecticide and tickicide and intermediate for production |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2034700A (en) * | 1978-10-27 | 1980-06-11 | Ici Ltd | Halogenated esters of cyclopropane acids, their preparation compositions and use as pesticides |
| EP0010859B1 (de) * | 1978-10-31 | 1982-12-01 | Imperial Chemical Industries Plc | Verfahren zum Herstellen von Cyclopropancarbonsäure-Estern |
| DE3111644A1 (de) * | 1981-03-25 | 1982-10-07 | Bayer Ag, 5090 Leverkusen | Phenoxypyridylmethylester, verfahren zu ihrer herstellung und ihre verwendung in schaedlingsbekaempfungsmitteln |
| FR2569189B1 (fr) * | 1984-08-14 | 1986-12-19 | Roussel Uclaf | Nouveaux derives du pyrrole, leur procede de preparation et leur application comme pesticides |
| US4582921A (en) * | 1984-09-17 | 1986-04-15 | University Of Iowa Research Foundation | Method of preparation of compounds containing perfluoroalkyl groups |
| EP0311565A1 (de) * | 1987-10-06 | 1989-04-12 | Ciba-Geigy Ag | Schädlingsbekämpfungsmittel |
-
1988
- 1988-03-31 FR FR8804260A patent/FR2629452B1/fr not_active Expired - Fee Related
-
1989
- 1989-03-16 ZA ZA892010A patent/ZA892010B/xx unknown
- 1989-03-29 MX MX015440A patent/MX173047B/es unknown
- 1989-03-30 DE DE89400887T patent/DE68906703T2/de not_active Expired - Lifetime
- 1989-03-30 US US07/331,732 patent/US4920231A/en not_active Expired - Fee Related
- 1989-03-30 AU AU32285/89A patent/AU622160B2/en not_active Ceased
- 1989-03-30 BR BR898901489A patent/BR8901489A/pt not_active IP Right Cessation
- 1989-03-30 AT AT91117775T patent/ATE129999T1/de not_active IP Right Cessation
- 1989-03-30 ES ES198989400887T patent/ES2042021T3/es not_active Expired - Lifetime
- 1989-03-30 NZ NZ228536A patent/NZ228536A/en unknown
- 1989-03-30 ES ES91117775T patent/ES2079015T3/es not_active Expired - Lifetime
- 1989-03-30 IE IE100589A patent/IE63711B1/en not_active IP Right Cessation
- 1989-03-30 EP EP91117775A patent/EP0476708B1/de not_active Expired - Lifetime
- 1989-03-30 DE DE68924786T patent/DE68924786T2/de not_active Expired - Fee Related
- 1989-03-30 EP EP89400887A patent/EP0335801B1/de not_active Expired - Lifetime
- 1989-03-31 JP JP1078715A patent/JPH026436A/ja active Pending
- 1989-03-31 CN CN89101909A patent/CN1023476C/zh not_active Expired - Fee Related
-
1990
- 1990-01-18 US US07/467,040 patent/US5089511A/en not_active Expired - Fee Related
-
1993
- 1993-07-07 GR GR920402859T patent/GR3008401T3/el unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55154943A (en) * | 1979-05-23 | 1980-12-02 | Bayer Ag | 22phenyllalkk11enyllcyclopropaneecarboxylic acid ester* its manufacture* use as insecticide and tickicide and intermediate for production |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3228589A (en) | 1989-10-05 |
| CN1023476C (zh) | 1994-01-12 |
| DE68906703D1 (de) | 1993-07-01 |
| EP0476708B1 (de) | 1995-11-08 |
| US4920231A (en) | 1990-04-24 |
| ATE129999T1 (de) | 1995-11-15 |
| ES2042021T3 (es) | 1993-12-01 |
| MX173047B (es) | 1994-01-31 |
| EP0335801A2 (de) | 1989-10-04 |
| EP0335801A3 (en) | 1989-12-06 |
| IE891005L (en) | 1989-09-30 |
| FR2629452B1 (fr) | 1990-11-09 |
| AU622160B2 (en) | 1992-04-02 |
| US5089511A (en) | 1992-02-18 |
| BR8901489A (pt) | 1989-11-14 |
| ZA892010B (en) | 1990-05-30 |
| EP0335801B1 (de) | 1993-05-26 |
| DE68906703T2 (de) | 1993-10-28 |
| CN1036561A (zh) | 1989-10-25 |
| DE68924786T2 (de) | 1996-04-18 |
| EP0476708A1 (de) | 1992-03-25 |
| DE68924786D1 (de) | 1995-12-14 |
| ES2079015T3 (es) | 1996-01-01 |
| NZ228536A (en) | 1991-07-26 |
| GR3008401T3 (de) | 1993-10-29 |
| FR2629452A1 (fr) | 1989-10-06 |
| IE63711B1 (en) | 1995-05-31 |
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